Sodium Bicarbonate → HCID 178488449, compound

HRID 513856

Reaction equation

HRID 513856 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:16]=[CH:15][C:10]3[NH:11][C:12]([CH3:14])=[N:13][C:9]=3[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([C:19]1[N:20]([S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[C:21]2[C:26]([CH:27]=1)=[CH:25][C:24](Br)=[CH:23][CH:22]=2)=[O:18].[CH3:39][O:40][C:41]1[CH:46]=[CH:45][C:44](B(O)O)=[CH:43][N:42]=1.C(=O)(O)[O-].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[NH2:1][C:2]1[N:6]([C:7]2[CH:16]=[CH:15][C:10]3[NH:11][C:12]([CH3:14])=[N:13][C:9]=3[CH:8]=2)[N:5]=[CH:4][C:3]=1[C:17]([C:19]1[N:20]([S:29]([C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[C:21]2[C:26]([CH:27]=1)=[CH:25][C:24]([C:44]1[CH:43]=[N:42][C:41]([O:40][CH3:39])=[CH:46][CH:45]=1)=[CH:23][CH:22]=2)=[O:18]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734368(6-Methoxypyridin-3-yl)boronic acidHCID 178427384HCID 178427384, compound

Product 1

HCID 178488449HCID 178488449, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of dioxane (0.6 ml), [5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-[5-bromo-1-(toluene-4-sulfonyl)-1H-indol-2-yl]-methanone (60 mg, 0.102 mmol), dichlorobis(triphenylphosphine)palladium (II) (14 mg, 0.020 mmol), 2-methoxy-5-pyridine boronic acid (39 mg, 0.255 mmol), and an aqueous solution of 2 M sodium bicarbonate (0.255 mL, 0.51 mmol) was stirred at 140° C. for six minutes in a microwave reactor. The reaction mixture was filtered through Celite, and washed with ethyl acetate and then with methanol. The filtrate was dried over anhydrous sodium sulfate. The desiccant was removed by filtration and concentration was performed. The residue obtained was purified by amino gel chromatography (dichloromethane/methanol=99/1 to 92/8). Thus, [5-amino-1-(2-methyl-1H-benzimidazol-5-yl)-1H-pyrazol-4-yl]-[5-(6-methoxy-pyridin-3-yl)-1-(toluene-4-sulfonyl)-1H-indol-2-yl]-methanone was obtained as a pale yellow solid (54 mg, 85%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. washwashed with ethyl acetate
  3. dry with materialThe filtrate was dried over anhydrous sodium sulfate
  4. customThe desiccant was removed by filtration and concentration
  5. customThe residue obtained
  6. customwas purified by amino gel chromatography (dichloromethane/methanol=99/1 to 92/8)

Sources & evidence

ORD record
ord-f3991858f39d4ed38e33881d2282c974
Source dataset
uspto-grants-2015_08
Patent number
US09102692B2

Linked notes

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